5. 1985-86 Edmonton Oilers
The Edmonton Oilers had won back-to-back Stanley Cups and were trying to join the Montreal Canadiens (four straight Cups from 1976 to ‘1979) and New York Islanders (1980 to 1983) in the list of teams that successful three-peated over the past decade.
Edmonton won the Presidents’ Trophy after compiling a record of 56-17-7, good for 119 points. They led the NHL with 426 goals for in the regular season. Wayne Gretzky led the way with 52 goals and a single-season record of 215 points. The Great One ran away with both the scoring title and the Hart Trophy.
This Edmonton team, loaded with future Hall of Famers, had four 100-point players. That didn’t include franchise icon Mark Messier, who finished with 35 goals and 84 points. Goalie Grant Fuhr posted a superb 29-8-0 record.
The Oilers finished with more points than the 1984-85 team that won the Stanley Cup. Heading into the postseason, it was easy to believe that Edmonton’s biggest enemy was itself. They just had to play their game and not give anything away. Sure enough, that ended up happening.
Edmonton swept Vancouver in the first round of the playoffs, and they went advanced to round two — taking on the arch-rival Calgary Flames. The Oilers had finished with 30 more points in the regular season, and it should have been an easy series victory.
But in the waning minutes of Game 7, Edmonton blueliner Steve Smith (on his birthday, mind you), accidentally banked the puck off Fuhr’s skate and into the net. Smith’s errant past would be the difference maker, and Calgary pulled off the stunning upset.
Well, Smith and the Oilers would go on to win the Stanley Cup in 1987, ’88 and ’90. So he redeemed himself just fine. But the Oilers would also never accomplish the three-peat, as one of the most dominant regular seasons ever wound up being all for nothing.